Podcast episode
Challenger Sales Mistakes | Dan Flood | 30MPC Hall of Fame
30 Minutes to President's Club3 Mar 202535 min
Description
ACTIONABLE TAKEAWAYS: Provide Hypotheses, Not Generic Questions: Instead of broad questions, offer informed hypotheses to invite deeper discussion. Ask Questions to Guide Next Steps: Use questions to guide the process without being pushy, keeping the prospect engaged. Teach Process Over Just Problems: Beyond identifying issues, recommend processes (like a custom demo over a POC) to build trust. Uncover Intent Behind Extra Steps: When extra steps are requested, ask what they aim to learn to suggest simpler options. DAN'S PATH TO PRESIDENTS CLUB: Senior Vice President of Global Sales @ Challenger VP of Sales, Account Management @ Challenger VP of Sales, Major Accounts @ Challenger Managing Vice President, Sales & Community @ Evanta RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal 30MPC Training: 30mpc.com/training
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at the end of that, you might reserve 10 minutes at the end of your call to say, Hey, look, we can spend hours on this demo. I could take you through this for the next several hours and deep dive into everything, but I want to pause and actually just ask, how is this landing? And in particular, I'm really curious to know where you see this working and what you're skeptical about. They'll tell you right out of the gate, right? “Because what you're trying to do is get the seeds of objections out very early.” So you can help work on those later on. If you don't do that, those objections are going to sit and brew and continue to grow over time. And that's what leads to people ghosting you later on. Today's show is brought to you by Insightly. Insightly is a CRM that helps you spot deal risk early, so pipe reviews actually drive
skeptical about. They'll tell you right out of the gate, right? Because what you're trying to do is get the seeds of objections out very early. So you can help work on those later on. If you don't do that, those objections are going to sit and brew and continue to grow over time. “And that's what leads to people ghosting you later on.” Today's show is brought to you by Insightly. Insightly is a CRM that helps you spot deal risk early, so pipe reviews actually drive your number. One question I ask in nearly every deal review is, what do we need to get in our next interaction with the customer? If my rep can't answer that question, the deal has risk, and I have something I can coach to.
What do you look for to determine that you have a real opportunity in front of you? One of the things that we talk about at Challenger is being able to quickly disqualify bad opportunities. So you're not wasting your time on them for months, but how do you do that? One of the things that we talk to our sellers about is leading with a “hypothesis and presenting a teaching moment right out of the gate to your buyer.” For us, what that might sound like is we help improve sales effectiveness for enterprise sales organizations. If you're a head of sales and your sales are lagging, you might say we need more pipeline, right? We just need a lot more at bats for our sellers. Our conversion rate is whatever it is, 20%. And so if I get X amount more pipe, that's going to make it happen.
And if I hear something like, oh, you know what? They get it. They're bought in on Challenger. They love it. This is more of a check the box kind of exercise, but they're all in, they get it. That to me is a major red flag because people don't buy on getting it or liking a solution. “They buy on how your solution is going to drive the economics of their business.” So being able to ask, does your CFO have a clear understanding of the ROI of this investment? Has your CFO seen this proposal before? Do they even know that this is coming? That can also be really telling because if they're like, no, I've got to bring them up to speed. Whoa, okay.
If this goes really well, here's what that would cost. Are you prepared to do that? If we meet whatever the success criteria of the proof of concept is, and a lot of times you can just walk yourself out of that proof of concept idea by going there because you end up talking about the full solution anyways, or you better qualify the larger opportunity “on what happens after the POC is done.” Dan, this has been a phenomenal episode, but the clock is ticking. We're running out of time and we got to move to the final question. We've talked about a lot of really great things salespeople should be doing. Now we got to flip that question on its head and ask you about a shouldn't. What is one bad habit that you see a lot of salespeople exhibiting that you think they need to break because it hurts them more than it helps? Okay.